O-diaminophosphinyl derivatives of oximes as urease inhibitors

Abstract

The invention relates to novel urease inhibited fertilizer compositions containing urea and a urease inhibiting amount of one or more o-diaminophosphinyl derivatives of oximes, and methods and composition for inhibiting the activity of urease through use of such compounds.

What is claimed is: 
     
       1. A urease inhibiting composition comprising a carrier and a urease inhibiting effective amount of one or more compounds of the formula: ##STR6## wherein: X is oxygen or sulfur; R 1  and R 2  are the same or different and are hydrogen, substituted or unsubstituted alkyl or aryl groups or R 1  and R 2  together may form a substituted or unsubstituted divalent aliphatic chain completing a cycloaliphatic group, which may optionally include one or more divalent heteroatoms of oxygen, sulfur or nitrogen wherein permissible substituents include one or more alkyl, aryl, halogen, trihalomethyl, nitro, cyano, alkanoyl, alkyl, carboxylate, arylcarboxylate, alkoxy, hydroxy, alkylmercapto, arylmercapto, mercapto, amino, alkylamino, dialkylamino, arylamino, diarylamino, diaminophosphinyl, N-diaminophosphinyl, O-diaminophosphinyl, S-diaminophosphinyl, carbamoyl and carbamoyldiaminophosphinyl; and   R 3 , R 4 , R 5  and R 6  are the same or different and are hydrogen or alkyl having from about 1 to about 4 carbon atoms.   
     
     
       2. A composition according to claim 1 wherein said urease inhibiting amounts is at least about 0.00001 weight percent based on the total weight of the composition. 
     
     
       3. A composition according to claim 2 wherein said amount is from about 0.0001 to about 98 weight percent. 
     
     
       4. A composition according to claim 3 wherein said amount is from about 0.002 to about 50 weight percent. 
     
     
       5. A composition according to claim 4 wherein said amount is from about 0.01 to about 20 weight percent. 
     
     
       6. A composition according to claim 1 wherein X is oxygen. 
     
     
       7. A composition according to claim 1 wherein X is sulfur. 
     
     
       8. A composition according to claim 1 wherein R 3 , R 4 , R 5  and R 6  are hydrogen. 
     
     
       9. A composition according to claim 1 wherein R 1  and R 2  are the same or different and are hydrogen, or substituted or unsubstituted alkyl or aryl, or R 1  and R 2  together form a cycloaliphatic group. 
     
     
       10. A composition according to claim 9 wherein R 1  and R 2  together form a cycloaliphatic group. 
     
     
       11. A composition according to claim 9 wherein R 1  and R 2  are the same or different and are hydrogen, or unsubstituted aryl or alkyl. 
     
     
       12. A composition according to claim 11 wherein R 1  and R 2  are the same or different and are hydrogen, aryl or primary alkyl provided that at least one of R 1  and R 2  is a primary alkyl or hydrogen. 
     
     
       13. A composition according to claim 12 wherein R 1  is hydrogen and R 2  is alkyl or aryl. 
     
     
       14. A composition according to claim 13 wherein R 2  is phenyl or alkyl having from about 1 to about 8 carbon atoms. 
     
     
       15. A composition according to claim 14 wherein R 2  is primary alkyl having from 1 to about 8 carbon atoms. 
     
     
       16. A composition according to claim 12 wherein R 1  is alkyl and R 2  is alkyl or aryl. 
     
     
       17. A composition according to claim 16 wherein R 2  is alkyl. 
     
     
       18. A composition according to claim 17 wherein R 2  is aryl. 
     
     
       19. A composition according to claim 1 which comprises a urease inhibiting effective amount of O-(diaminophosphinyl)-2-propanone oxime. 
     
     
       20. A fertilizer composition which comprises urea and/or one or more urea precursor compounds capable of forming urea in situ when subjected to the use conditions of the composition, and a urease inhibiting effective amount of one or more compounds of the formula: ##STR7## wherein: X is oxygen or sulfur; R 1  and R 2  are the same or different and are hydrogen, substituted or unsubstituted alkyl or aryl groups or R 1  and R 2  together may form a substituted or unsubstituted divalent aliphatic chain completing a cycloaliphatic group, which may optionally include one or more divalent heteroatoms of oxygen, sulfur or nitrogen wherein permissible substituents include one or more alkyl, aryl, halogen, trihalomethyl, nitro, cyano, alkanoyl, alkyl, carboxylate, arylcarboxylate, alkoxy, hydroxy, alkylmercapto, arylmercapto, mercapto, amino, alkylamino, dialkylamino, arylamino, diarylamino, diaminophosphinyl, N-diaminophosphinyl, O-diaminophosphinyl, S-diaminophosphinyl, carbamoyl and carbamoyldiaminophosphinyl; and   R 3 , R 4 , R 5  and R 6  are the same or different and are hydrogen or alkyl having from about 1 to about 4 carbon atoms.   
     
     
       21. A composition according to claim 20 wherein X is oxygen. 
     
     
       22. A composition according to claim 20 wherein X is sulfur. 
     
     
       23. A composition according to claim 20 wherein R 3 , R 4 , R 5  and R 6  are hydrogen. 
     
     
       24. A composition according to claim 20 wherein R 1  and R 2  are the same or different and are hydrogen, or substituted or unsubstituted alkyl or aryl, or R 1  or R 2  together form a cycloaliphatic group. 
     
     
       25. A composition according to claim 24 wherein R 1  and R 2  are the same or different and are hydrogen, or unsubstituted aryl or alkyl. 
     
     
       26. A composition according to claim 25 wherein R 1  and R 2  are the same or different and are hydrogen, aryl or primary alkyl provided that at least one of R 1  and R 2  is primary alkyl or hydrogen. 
     
     
       27. A composition according to claim 26 wherein R 1  is hydrogen or alkyl and R 2  is alkyl or aryl. 
     
     
       28. A composition according to claim 27 wherein R 2  is phenyl or alkyl. 
     
     
       29. A composition according to claim 28 wherein R 2  is alkyl having from 1 to about 8 carbon atoms. 
     
     
       30. A composition according to claim 20 which comprises a urease inhibiting effective amount of O-(diaminophosphinyl)-2-propanone oxime. 
     
     
       31. A compound of the formula: ##STR8## wherein: X is oxygen or sulfur; R 1  and R 2  are the same or different and are hydrogen, substituted or unsubstituted alkyl or aryl groups or R 1  and R 2  together may form a substituted or unsubstituted divalent aliphatic chain completing a cycloaliphatic group, which may optionally include one or more divalent heteroatoms of oxygen, sulfur or nitrogen wherein permissible substituents include one or more alkyl, aryl, halogen, trihalomethyl, nitro, cyano, alkanoyl, alkyl, carboxylate, arylcarboxylate, alkoxy, hydroxy, alkylmercapto, arylmercapto, mercapto, amino, alkylamino, dialkylamino, arylamino, diarylamino, diaminophosphinyl, N-diaminophosphinyl, O-diaminophosphinyl, S-diaminophosphinyl, carbamoyl and carbamoyldiaminophosphinyl; and   R 3 , R 4 , R 5  and R 6  are the same or different and are hydrogen or alkyl having from about 1 to about 4 carbon atoms.